Silicone monomers and oligomers having a carboxyl functional group thereon

ABSTRACT

Organosilane and organosiloxane monomers are provided containing at least one carboxyl ester functional group represented by the formula: ##STR1## wherein: R which can be the same or different are hydrolyzable groups; 
     R 1  which can be the same or different, are selected from substituted or unsubstituted alkyl, cycloalkyl, substituted or unsubstituted aryl, alkenyl, alkynyl or --OS i  (R 1 ) 3  ; 
     x is zero to 3; 
     R 2  is linear or branched alkylene of 1-12 carbon atoms; 
     B is --NR 6 , sulfur or oxygen; 
     R 6  is hydrogen or alkyl; 
     n 1  is zero or 1; 
     F is linear or branched alkylene of 1-10 carbon atoms; 
     n is zero or 1, with the proviso that if n 1  is 1, n is 1 and if n 1  is 0, n is 0; 
     R 3  is ##STR2## R 5  is alkyl or trialkylsilyl.

FIELD OF THE INVENTION

The present invention relates to organosilane and organosiliconecompounds and, more particularly, to novel organosilane compounds andorganosiloxane compounds and oligomers containing a functional carboxylgroup and to a method of making the same.

BACKGROUND OF THE INVENTION

Various organosilane and organosiloxane monomers or compounds includingorganosiloxane oligomers containing one or more organofunctional groupssuch as amines, vinyls, mercaptans, epoxies, halogens, and the like arewidely known. These compounds have been used in a variety of ways suchas coupling agents and adhesion promoters for inorganic materials, asreactants for modifying the properties of organic polymers, ascrosslinking agents for curable organic polymer systems, as additivesfor a variety of home care and personal care compositions, as well asmonomers for the preparation of silicon containing polymers.

While silane and siloxane monomers containing a variety oforganofunctional groups are well known and can be readily prepared,organosilane and organosiloxane monomers containing functional carboxylgroups are generally not available commercially. Heretofore, noconvenient method for preparing such monomers with carboxyl functionalgroups has been known and indirect procedures would generally have to beused for their preparation. Accordingly, the development of organosilaneand organosiloxane monomers or compounds containing one or moreorganofunctional carboxyl groups and methods for readily preparing thesecompounds would be desirable, It would be particularly advantageous ifmethods for preparing such compounds not only employed readily availablematerials, but carboxyl-functional organosilicone monomers and oligomerscould be prepared containing other functional groups as well, such ashalogen groups, which makes possible the preparation of a variety oforganosilicone derivatives including oligomers thereof.

While, as indicated, organosilane and organosiloxane compoundscontaining a variety of functional groups and methods for preparing thesame, heretofore, have been known and used, there is no known disclosureor suggestion of the novel carboxyl-functional organosilane andorganosiloxane compounds and oligomers of the present invention or ofthe method for making the same herein described.

SUMMARY OF THE INVENTION

It is accordingly an object of the present invention to provide a novelclass of organosilane and organosiloxane compounds having at least onefunctional carboxylic ester group thereon and which may also include avariety of other functional groups as well.

It is another object of the present invention to provide a novel classof organosilane and organosiloxane compounds having a novel type ofpyrrolidone-containing carboxylic ester functional group thereon and mayalso include other functional groups as well.

It is yet another object of the present invention to provide a novelclass of organosiloxane compounds and oligomers having at least onefunctional carboxylic ester group thereon.

It is a further object of the present invention to provide a process forreadily producing organosilane and organosiloxane compounds containingat least one carboxylic ester functional group.

These and other objects will become apparent from the dscription tofollow.

In accordance with the present invention, there has now been discoverednovel organosilane and organosiloxane compounds containing one or morefunctional carboxylic ester group(s) that may be represented by thefollowing general formula: ##STR3## wherein: R, which can be the same ordifferent, are hydrolyzable groups such as but not limited to halogen,acyloxy, N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkenyl,alkynyl or --O--Si--(R¹)₃ ;

x can be zero to 3;

R² is linear or branched alkylene of 1-12 carbon atoms, preferablymethylene;

B is --NR⁶, sulfur or oxygen;

R⁶ is H or alkyl (C₁₋₂₀);

n¹ is zero or 1;

F is linear or branched alkylene of 1-10 carbon atoms, preferablyethylene;

n is zero or 1, with the proviso that if n¹ is 1, n is 1 and if n¹ is 0,n is 0;

R³ is ##STR4## R⁵ is alkyl (C₁₋₂₀) or trialkysilyl.

In another aspect of the present invention there are provided novelorganosiloxane compounds and oligomers containing one or more functionalcarboxylic ester groups that may be represented by the formula: ##STR5##wherein: R^(a) which can be the same or different, are hydrolyzablegroups such as but not limited to halogen, hydroxy, alkoxy,alkoxyalkoxy, acyloxy, N, N-dialkylaminoxy, N-alkylamido,monoalkylamino, dialkylamino, isocyanato, alkylthio or cyano;

R¹ are as hereinabove defined;

R⁷ and R⁸, which may be the same or different, are selected from alkyl,aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenylor alkynyl;

M can be the same or different and is selected from hydrogen, R^(a), R¹and --CH₂ --CHR⁶ --R² --B_(n) ¹ --F_(n) --R³, with the proviso that atleast one M is --CH₂ --CHR⁶ --R² --B_(n) ¹ --F_(n) --R³ ;

y can be zero to 2;

a is from zero to 10;

b is from zero to 10;

R², R³, R⁵, B, F, n and n¹ are as defined hereinabove.

In yet another aspect of the present invention there is provided amethod for preparing organosilane or organosiloxane monomers containingone or more pyrrolidone-containing functional carboxyl ester groupswhich comprises reacting a N-alkenyl pyrrolidone containing acarboalkoxyl group of the formula

    CH.sub.2 ═CR.sup.6 --R.sup.2 --B.sub.n1 --F.sub.n --R.sup.3

wherein:

R², R³, R⁶, F, B, n¹ and n are as hereinabove defined.

with an organosilane hydride having one or more hydride groups of theformula ##STR6## wherein: R^(b), which can be the same or different, arehydrolyzable groups such as but not limited to halogen, alkoxy,alkoxyalkoxy, acyloxy, N,N-Dialkylaminoxy, N-alkylamido, monoalkylamino,dialkylamino,isocyanato, alkylthio or cyano;

R¹ and x are as hereinabove defined.

at an elevated temperature (preferably between 65° C. and 130° C.) inthe presence of a noble metal catalyst for a time sufficient to reactthe hydride group(s) on the silicon atom with the olefinic group on thepyrrolidone.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

In accordance with the present invention there are provided novelorganosilane and organosiloxane monomers or compounds containing acarboxylic ester functional group which may be represented by thegeneral formula: ##STR7## wherein: R which can be the same or different,are hydrolyzable groups such as but not limited to halogen, acyloxy,N,N-Dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, preferably lower alkyl (C₁ -C₆);cycloalkyl,e.g. cycloheptyl;aralkyl, e.g. benzyl,phenylethyl etc.; substituted or unsubstitutedaryl;alkenyl; alkynyl or --OSi(R¹)₃ ;

x can be zero to 3;

R² is linear or branched alkylene of 1-12 carbon atoms, preferablymethylene;

B is --NR⁶, sulfur or oxygen;

R⁶ is H or alkyl (C₁₋₂₀), preferably hydrogen or methyl;

n¹ is zero or 1;

F is linear or branched alkylene of 1-10 carbon atoms, preferablyethylene;

n is zero or 1, with the proviso that if n¹ is 1, n is 1 and if n¹ is 0,n is 0;

R³ is ##STR8## R₅ is alkyl (C₁₋₂₀), preferably lower alkyl (C₁₋₆) ortrialkylsilyl.

In accordance with the present invention there are also providedorganosiloxane compounds and oligomers containing one or more functionalcarboxyl groups that may be represented by the formula: ##STR9##wherein: R^(a), which can be the same or different, are hydrolyzablegroups such as but not limited to halogen, hydroxy,alkoxy, alkoxyalkoxy,acyloxy, N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkenyl,alkynyl or --O--Si--(R¹)₃ ;

R⁷ and R⁸, which may be the same or different, are selected from alkyl,aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenylor alkynyl;

M can be the same or different and is selected from hydrogen, R^(a), R¹and --CH₂ --CHR₆ --R² --B_(n) ¹ --F_(n) --R³ , with the proviso that atleast one M group is --CH₂ --CHR⁶ --R² --B_(n) ¹ --F_(n) --R³ ;

y can be zero to 2;

a is from zero to 10;

b is from zero to 10;

R², R³, R⁵, B, F, n and n¹ are as defined hereinabove.

The novel carboxylic ester functional organosilane and organosiloxanemonomers of the present invention surprisingly and unexpectedly can bereadily prepared by reacting a silane monomer having one or more hydridesubstituents on the silicon atom of the formula: ##STR10## with apyrrolidone nucleus containing a N-monosubstituted terminal olefinicgroup of the formula:

    CH.sub.2 ═CR.sup.6 --R.sup.2 --B.sub.n.sup.1 --F.sub.n --R.sup.3

wherein:

R^(b) which can be the same or different, are hydrolyzable groups suchas but not limited to halogen, alkoxy, alkoxyalkoxy, acyloxy,N,N-Dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, preferably lower alkyl (C₁ -C₆); cycloalkyl, e.g. cycloheptyl;aralkyl, e.g. benzyl, phenylethyl etc.; substituted or unsubstitutedaryl; alkenyl; alkynyl or --OSi(R¹)₃ ;

x can be zero to 3;

R² is linear or branched alkylene of 1-12 carbon atoms, preferablymethylene;

B is --NR⁶, sulfur or oxygen;

R⁶ is H or alkyl (C₁₋₂₀); preferably hydrogen or methyl;

n¹ is zero or 1;

F is linear or branched alkylene of 1-10 carbon atoms, preferablyethylene;

n is zero or 1, with the proviso that if n¹ is 1, n is 1 and if n¹ is 0,n is 0;

R³ is ##STR11## R⁵ is alkyl, preferably lower alkyl (C₁₋₆) ortrialkylsilyl.

The reaction is carried out in the presence of a noble metal (Group VIIImetal) catalyst, preferably soluble platinum, at an elevated temperature(65° C. to 130° C.) for a time sufficient for substantially all of theN-alkenyl carboalkoxy containing pyrrolidone to react with the hydridegroup(s).

The reaction can be carried out neat or in inert solvents such astoluene, benzene, chlorobenzene, heptane and the like. In general, fromabout 0.5, preferably from about 0.9 to 1.1 equivalents of the N-alkenylcarboalkoxy containing pyrrolidone groups per functional hydride groupsis reacted with the hydride groups of the silane monomer, whereinsubstantially all the N-alkenyl carboalkoxy containing pyrrolidone and,preferably all of the functional hydride group(s) are reacted and anorganosilane or organosiloxane compound with at least onepyrrolidone-containing functional-carboxylic ester group(s), is formed.The reaction is carried out in the presence of a noble metal catalyst.Suitable platinum catalysts include solubilized platinum or platinummetal on supports such as alumina, charcoal and the like. In generalfrom about 10⁻³ to 10⁻⁶ moles of platinum per mole of hydride group canbe used.

The carboalkoxy containing pyrrolidone reactant suitable for use inaccordance with the practice of the present invention may be prepared bythe reaction of an olefinic amine having a functional primary aminegroup(s) of the formula:

    CH.sub.2 ═CR.sup.6 --R.sup.2 --B.sub.n.sup.1 --F.sub.n --NH.sub.2

wherein:

R² is linear or branched alkylene of 1-12 carbon atoms, preferablymethylene;

B is --NR⁶, sulfur or oxygen;

R⁶ is H or alkyl, preferably hydrogen or methyl;

F is linear or branched alkylene 1-10 carbon atoms, preferably ethylene;

n is zero or 1; and

n¹ is zero or 1, with the provisio that if n¹ is 1, n is 1 and if n¹ is0, n is 0;

with up to about one equivalent, preferably about stoichiometricquantities, of itaconic ester per primary amine group at an elevatedtemperature for a time sufficient for substantially all of the itaconicester to react with the primary amine group(s) and the formation ofpyrrolidone containing a carboalkoxyl functional group(s).

Itaconic acid (methylene succinic acid) and/or ester is a compound ofthe formula:

    CH.sub.2 ═C(COOR.sup.6)--CH.sub.2 --COOR.sup.6

wherein

R⁶, which can be the same or different, is hydrogen or alkyl (C₁₋₂₀)preferably lower alkyl (1-6 carbon atoms).

The compound itaconic acid is available commercially from PfizerChemicals Division and Rhone Poulenc whereas ester derivatives thereofare available from Morflex, Inc., Greensboro, N.C. The compounds areproduced by known fermentation techniques although chemical synthesismethods are also known.

Olefinic amine compounds suitable for use are any olefinic aminesincluding diamines having at least one primary amine group of theformula:

    CH.sub.2 ═CR.sup.6 --R.sup.2 --B.sub.n1 --F.sub.n --NH.sub.2

wherein,

R², R⁶, B, F, n and n¹ are as hereinabove defined.

Exemplary suitable allyl amine compounds include allyl amine, methallylamine, allyloxypropyl amine, allylthiopropyl amine, methallyloxypropylamine and exemplary suitable allyl diamine compounds are N-allylethylene diamine, N-allyl propylene diamine and N-allyl, N-methylenepropylene diamine.

In general, from about 0.5, preferably from about 0.9 to about 1.1,equivalents of itaconic ester per functional primary amine group isreacted with the primary amine group of the olefinic amine compoundwherein substantially all of the itaconic and preferably all the primaryamine group(s) are reacted and an N-alkenyl carboalkoxy compoundcontaining a pyrrolidone nucleus is formed of the formula:

    CH.sub.2 ═CR.sup.6 --R.sup.2 --B.sub.n1 --F.sub.n --R.sup.3

wherein R², R⁶, B, F, R³, n¹ and n are as defined hereinabove.

The reaction can be carried out neat or in an inert solvent such asalcohol, hydrocarbon solvent, chlorinated hydrocarbon and the like, asdesired, in general at elevated temperatures up to about 175° C.,preferably from about 90° C. to about 130° C. The reaction readilyproceeds and generally complete reaction of the itaconic ester with theavailable primary amine group(s) occurs in the Michael Addition mannerwith the double bond of the itaconic ester followed by immediatecyclization to form a pyrrolidone group which will occur in from about 1to 5 hours.

In another aspect of the present invention, the novel organosiloxanecompounds and oligomers of the present invention can be readily preparedby reacting an organosiloxane compound or oligomer having one or morehydride groups on the silicone atoms of the forumla: ##STR12## wherein:R^(b), which can be the same or different, are hydrolyzable groups suchas but not limited to halogen, alkoxy, alkoxyalkoxy, acyloxy,N,N-dialkylaminoxy, N-alkylamido,monoalkylamino, dialkylamino,isocyanato, alkylthio or cyano;

R¹ which can be the same or different, are substituted or unsubstitutedalkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkenyl,alkynyl or --O--Si--(R¹)₃

R⁷ and R⁸, which may be the same or different, are selected from alkyl,aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenylor alkynyl;

N can be the same or different and is selected from hydrogen, R^(b) andR¹, with the proviso that at least one, N is hydrogen;

y can be zero to 2;

a is from zero to 10;

b is from zero to 10;

With an ester containing pyrrolidone nucleus containing aN-monosubstituted terminal olefinic group as hereinabove described. Thereaction is carried out as hereinabove described in the presence of anoble metal (Group VIII metal) catalyst, preferably soluble platinum, atan elevated temperature (65° to 130° C.) for a time sufficient forsubstantially all of the N-alkenylcarboalkoxy containing pyrrolidone toreact with the hydride group(s).

The organosilicone monomers according to the present invention areuseful, for example, as coupling agents and adhesion promoters forinorganic materials, as reactants for modifying the properties oforganic polymers, as crosslinking agents for curable organic polymers,as additives for personal and home care products, as precursors fororganic or organosilicone polymers of varying molecular weights and thelike.

The above is a general description of the present invention. Thefollowing examples are given for the purpose of illustration and are notintended in any way to limit the invention as claimed. Unless noted tothe contrary, proportions are on a weight basis.

EXAMPLE 1

This example illustrates the method for making N-allyl-4-carbomethoxypyrrolidone.

A solution of 158 grams of Dimethyl itaconate and 200 ml of methanol ischarged to a reaction vessel and 57 grams of allyl amine is addeddropwise to the itaconate solution with agitation in the reactionvessel. During addition of allyl amine to the reaction mixture, thetemperature increased from ambient to 62° C.

Upon complete addition of the allyl amine the reaction mixture is keptat reflux for 4 additional hours. The methanol is distilled from thereaction mixture and the reaction product is distilled at 115° C. underreduced pressure (1 mm). A yield of 92% is obtained. The structure ofthe reaction product is evaluated by IR.

EXAMPLE 2

This example illustrates the preparation of N-(Dimethylchlorosilylpropyl)-4-carbomethoxy pyrrolidone.

To 183 grams of N-allyl-4-carbomethoxy pyrrolidone prepared as describedin Example 1 and 1 ml of 0.1N-chloroplatinic acid in isopropanol chargedto a reaction vessel with agitation, 94.5 grams of Dimethyl chlorosilaneis added dropwise to the reaction mixture and an exotherm occursincreasing the reaction mixture temperature to 90°-95° C. The reactiontemperature is maintained at 95° C. for 4 hours after all the silanereactant is added to the reaction mixture. A colorless oil is obtainedby distilling at 168°-170° C. under 2 mm pressure with about 90% yield.The structure of the reaction product is confirmed by NMR and IR.

EXAMPLE 3

This example illustrates the preparation ofN-(Dichloromethylsilypropyl)-4-Carbomethoxy pyrrolidone.

A reaction mixture of 183 grams of N-allyl-4-carbomethoxy pyrrolidoneprepared as described in Example 1 and 1 ml of 0.1N chloroplatinic acidin isopropanol is charged to a reaction vessel. 115 grams ofmethyldichlorosilane is added dropwise to the reaction mixture withagitation during which an exothermic reaction occurs increasing thetemperature of the reaction mixture to 90°-95° C. The temperature of thereaction mixture is maintained at 95° C. for 4 hours after the additionof the silane is completed. The reaction mixture is distilled duringwhich a colorless oil is obtained at a temperature of 174°-176° C. under2 mm pressure. A yield of product of 93% is obtained and the structureis confirmed by IR and NMR.

EXAMPLE 4

This example illustrates the preparation ofN-(Triacetoxysilylpropyl)-4-carbomethoxy pyrrolidone.

A reaction mixture is prepared from 183 grams of N-allyl-4-carbomethoxyprepared as described in example 1 and 1 ml of 0.1N chloroplatinic acidin a reaction vessel. 206 grams of triacetoxysilane is added dropwise tothe reaction during which an exotherm is created increasing the reactionmixture to 110°-115° C. After all the silane reactant has been added,the temperature of the reaction mixture is maintained at 110° C. for 3hours. A low melting reaction product is recovered from the solidreaction vessel and the structure of the product is confirmed by NMR andIR.

EXAMPLE 5

This example illustrates the preparation of N- Bis(methylethylketoximino) methylsilylpropyl!-4-carbomethoxy pyrrolidone.

A reaction mixture is charged to a reaction vessel containing equalmolar amounts of Bis(methyl ethyl ketoximino) methyl silane andN-allyl-4-carbomethoxy pyrrolidone and about 10⁻⁴ moles ofchloroplatinic acid in isopropanol. The reaction mixture forms anexotherm of about 110° C. after which the reaction mixture is maintainedat 130° C. for 3 hours. The structure of the reaction product isconfirmed by NMR and IR.

EXAMPLE 6

This example illustrates the preparation of N-(Trichlorosilylpropyloxypropyl)-4-carbomethoxy pyrrolidone.

A reaction mixture of 236 grams of N-allyloxypropyl-4-carbomethoxypyrrolidone prepared by replacing allyl amine with allyloxypropyl amineas described in Example 1. 0.1N chloroplatinic acid and isopropanol ischarged to a reaction vessel and heated to about 85° C. 135.5 grams ofTrichlorosilane is added dropwise to the reaction mixture withagitation. The reaction mixture is exothermic and heat is removed tomaintain the temperature at about 90°-95° C. Upon adding all thetrichlorosilane, the reaction temperature is maintained at 120° C. for 2hours. Low boiling is materials are stripped from the reaction mixtureunder reduced pressure. A yield of 95% of product is obtained and thestructure of the reaction product is confirmed by I.R. and NMR.

EXAMPLE 7

The addition of methyldichlorosilane toN-(allylthiopropyl)-4-carbomethoxy pyrrolidone in the presence ofcatalytic amounts of chloroplatinic acid results in the formation ofN-(methyldichlorosilylpropylthiopropyl)-4-carbomethoxy pyrrolidone withyields and structure confirmed by G.C. analysis, I.R. and NMR.

EXAMPLE 8

Allyl methyl amine is cyanoethylated with acrylonitrile followed bypalladium catalyzed reaction with hydrogen to prepare the reactionproduct N-allyl, N-methyl, propylene diamine is identified by NMR andI.R.

Equimolar amounts of N-allyl, N-methyl, propylene diamine prepared asdescribed above and Dimethyl Itaconate are charged to a reaction vesseland heated slowly with agitation to 130°-150° C. After the exothermsubsides, the reaction mixture is maintained at 140° C. for 3 hours. Thereaction product 1-(N-allyl, N-methyl aminopropyl)-4-carbomethoxypyrrolidone is isolated by distillation.

Triethoxysilane is added dropwise to an equimolar amount of the1-(N-allyl, N-methyl aminopropyl)-4-Carbomethxyl pyrrolidone preparedabove in the presence of 0.1M chloroplatinic acid while maintaining areaction temperature of 120°-140° C. After completion of the reaction,the product is isolated by fractionation of the reaction mixture and theproduct is identified by NMR and I.R.

What is claimed is:
 1. Organosilane and organosiloxane monomers havingat least one carboxylic ester funtional group that is represented by theformula: ##STR13## wherein: R which can be the same or different arehydrolyzable groups;R¹ which can be the same or different, are selectedfrom substituted or unsubstituted alkyl, cycloalkyl, substituted orunsubstituted aryl, alkenyl, alkynyl or --OSi(R¹)₃ ; x is zero to 3; R²is linear or branched alkylene of 1-12 carbon atoms; B is --NR⁶, sulfuror oxygen; R⁶ is hydrogen or alkyl; n¹ is zero or 1; F is linear orbranched alkylene of 1-10 carbon atoms; n is zero or 1, with the provisothat if n¹ is 1, n is 1 and if n¹ is 0, n is 0; R³ is ##STR14## R₅ isalkyl or trialkylsilyl.
 2. The organosilane and organosiloxane monomersas claimed in claim 1, wherein R are hydrolyzable groups selected fromhalogen, acyloxy, N,N-Dialkyl-aminoxy, N-alkylamido, monoalkylamino,dialkylamino, isocyanato, alkylthio or cyano groups or mixtures of thesame.
 3. The organosilane and organosiloxane monomers as claimed inclaim 2, wherein R¹ is selected from substituted or unsubstituted loweralkyl, cycloalkyl, substituted or unsubstituted aryl, alkenyl, alkynylor --OSi(R¹)₃.
 4. The organosilane and organosiloxane mononers asclaimed in claim 2, wherein R₅ is lower alkyl or trialkylsilyl.
 5. Theorganosilane and organosiloxane monomers as claimed in claim 1, whereinn and n¹ are zero.
 6. The organosilane and organosiloxane monomers asclaimed in claim 2, wherein said compounds are an amphoteric class oforganosilicone compounds, B is --NR⁶ and R¹ is selected from substitutedor unsubstituted alkyl, substituted or unsubstituted aryl, alkenyl,alkynyl or --OS_(i) (R)₃.
 7. The organosilane and organosiloxanemonomers aa claimed in claim 1, wherein R¹ =--OSi(CH₃)₃ and x=1 to
 3. 8.The organosilane and organosiloxane monomers as claimed in claim 7,wherein R² is methylene, R⁶ is hydrogen or methyl, n=0 and n¹ =0.
 9. Themethod of preparing organosiloxane compounds having one or morepyrrolidone groups having functional carboxyl ester groups whichcomprises reacting a N-alkenyl pyrrolidone having a carboalkoxyl groupof the formula:

    CH.sub.2 ═CR.sup.6 R.sup.2 --B.sub.n1 --F.sub.n --R.sup.3

wherein: R² is a linear or branched alkylene of 1-12 carbon atoms; R⁶ ishydrogen or alkyl; F is linear or branched alkylene of 1-10 carbonatoms; B is --NR⁶, sulfur or oxygen; n¹ is zero or 1; n is zero or 1,with the proviso that if n¹ is 1, n is 1 and if n¹ is 0, n is 0; R³ is##STR15## R₅ is alkyl or trialkylsilyl; with an organosilane hydridegroup of the formula: ##STR16## wherein: R^(b) is selected from ahydrolyzable group; R¹ is selected from substituted or unsubstitutedalkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkeneyl,alkynyl or --O--Si--(R¹)₃ groups or mixtures of the same; x is from 0 to3;at an elevated temperature in the presence of a noble metal catalystfor a time sufficient to react the hydride groups on the silicone atomwith an olefinic group on the pyrrolidone.
 10. The method of preparingorganosiloxane compounds as claimed in claim 9, wherein R^(b) are thesame or different hydrolyzable group selected from halogen, alkoxy,alkoxyalkoxy acyloxy, N, N-Dialkylamoxy, N-alkylamido, monoalkylamino,dialkylamino, isocyanato, alkylthio, or cyano groups or mixtures of thesame.